Stereoselective toxicity of malathion and its metabolites, malaoxon and isomalathion

In recent years, the stereoselective toxicity of chiral organophosphorus pesticides has received increasing attention from environmental toxicology scientists. In an attempt to explore the stereoselective effects of chiral organophosphorus pesticides on non-target organisms and enzymes, this work investigated the stereoselective toxicity and inhibition of malathion, malaoxon and isomalathion on Daphnia magna and on acid alpha-naphthyl acetate esterase extracted from wheat flour, respectively. Toxicity differences were observed between the two enantiomers of malathion and malaoxon and among the four stereoisomers of isomalathion in the LC50 values on D. magna and the IC50 values on acid alpha-naphthyl acetate esterase. Enantiomers with (R)-configuration in all the tested compounds showed higher toxicity to D. magna than their (S)-forms and racemic forms. Racemic malaoxon and isomalathion showed the strongest inhibition on acid alpha-naphthyl acetate esterase compared to their respective enantiomers and stereoisomers.